


Teddy Bounce

by Zeath



Category: Homestuck
Genre: Anal Fingering, Anal Sex, And Lots of It, Blow Jobs, Choking, Come Swallowing, Dildos, Dirty Talk, Dirty Thoughts, Dry Humping, Incest, Lube, M/M, Masturbation, NSFW, Plushophilia, Rutting, Sex Toys, Sexual Fantasy, Sexual Humor, Sibling Incest, Size Kink, Strap-Ons, Stuffed Toys, Teasing, Teddy Bears, gagging
Language: English
Status: Completed
Published: 2015-12-04
Updated: 2015-12-23
Packaged: 2018-05-04 22:18:40
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 5,108
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5350472
Author URL: https://archiveofourown.org/users/Zeath/pseuds/Zeath
Summary: <blockquote class="userstuff">
              <p>"This time for sure, you will fit. So help me God.”</p><p>Dave is finally fulfilling his fantasy of fucking his teddy bear, and won't be deterred by a size a little too big.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> I got an ask so long ago about Dave riding and humping a teddy bear, so here you go anon, sorry about the SUPER late reply. 
> 
> Plushophilia is where someone is sexually or romantically attracted to a stuffed animal. If you are uncomfortable with that then don't read.

All through his young life, no matter if he wanted to be or not, Dave had always been around toys. Either they were stuffed, felt, cuddly buddies, creepy looking sex toys that his brother had made, or simply the puppets and dolls that were lounging around the apartment randomly, it didn’t matter. Maybe that was why he was so fucked up now; being influenced at a young age to be okay with sexual stuffed toys, because he had a fetish for it now. He could get off without it, no problems there, but nothing made him cum faster than finding a video of someone riding a teddy bear, or imagining himself humping against one until his balls were drained. He had tried to satisfy his need for felt a couple of times; a lonely smuppet, waiting for him to defile it with his cock. He had taken it to his room secretly and placed it on the bed, slipping his dick between the soft mounds of the smuppet’s rump and rutting until he came muffling his voice by biting into his pillow.

It was all sorted out now. Dave had thought it through a number of times, going online and ordered the biggest strap on he could find, it cost a big wad of his earnings but it would be worth it in the end. He had remembered his brother’s advice; it doesn’t matter about the price as long as it’s going to work up to standards. Funny, Bro probably thought it would be about video games or some shit, definitely not a sex toy he would be strapping onto a toy for him to bounce on. Speaking of his brother, he doesn’t know if Bro knows by now about his fetish, the walls are pretty thin and it wouldn’t be hard with his sneaking skills to find out. Dave didn’t care, it may be embarrassing in the long run but the teenager’s mind-set was too prepared about the main event to think about precautions.

Dave had also made sure to get a big bear, and when he meant big, he meant huge. He knew he had one shoved into the apartment’s small attic from when he was a child, and so without further ado, Dave collected it and pulled it out. Digging it out was one thing, but it was old and covered in dust and cobwebs, it’s once faux fur losing its tan. It didn’t take much to get the bear into better shape, just some cleaning and sprucing up the fur, even finishing off the look with a big blue ribbon around the bear’s fluffy neck. It was obvious that Bro saw him; it was kind of hard to miss making all that noise just to get the seven foot tall bear down from a tiny attic, let alone the racket of fussing around to fix the toy up to his standards. But Bro didn’t say anything, letting his little brother do what he wanted because who was he to judge?

He couldn’t help himself that night, dragging the bear up onto his bed and stripping bare. Dave rubbed one out with his legs straddling the giant teddy, an arm looping round its thick neck and clinging to it as his other hand strangled his cock for all it was worth, pumping steadily. He loved the feel of the soft fur against his skin, able to hold onto the bear and let himself be swallowed into his fantasy; the squishy fluff tickled his thighs as they trembled, his member making slick noises as his hand sped up.

He doesn’t know what it was about his fetish, maybe it was the cute face and a soft body to hold onto like an everlasting partner? Albeit a very fuzzy one. Or perhaps it was all about not being alone? Dave was always on his own when he was a child, surrounded by his brother, danger, and toys. Whatever it was, he was stuck with this now, the insistent need for something to fill him up in all the right ways, along with holding onto something soft between his fingers. It’s all he’ll ever want. He slept with the bear every night, stripping himself naked and cuddling up with the fluffy beast, slugging his leg over the giant so he could rub his hairless cock against the faux fur. After the third week of waiting, his order arrived in the mail, a medium sized package left outside their door for anyone to see. He was lucky that he got to it first, because having Bro find out what exactly he bought would have just been humiliating. Taking it to his room and setting it on his bed, Dave opened it up and shivered at the size of it.

The thick girth could almost match the same size as his forearm, and the length was something to be feared, almost hitting twelve inches. He knew he had to prepare himself a lot before even attempting to fit the tip inside. Digging around the box a little more, Dave spotted a large bottle of lube, not that he needed it; he had already gotten one, but he was glad that the extra help was there. In a little complimentary package, there was one tiny sized dildo at the bottom of the box attached to a thank you note from the website he ordered from. The little dick wasn’t much, but he could still get off on it if he just wanted to feel a stretch around his fluttering hole.

Setting the dildo aside for the moment and nudging the box over the edge of the bed, Dave got to work with the gear of the strap on, getting used to the feel of it. The strap on basically looked like a rock climbing harness, with little connections so he could loosen and tighten to sides to better suit the person using it. Dave dragged it over to the teddy bear and slotted the furry legs through the harness, sliding it up and to its crotch with a little struggle and tightening it up once it was set in place. He sat back and admired his work, it did look kind of ridiculous; his childhood bear with a massive cock strapped onto it. Still, it wasn’t about looks, and anyway he would be clinging onto the toy like his life depended on it later on.

Of course he was nervous, the size was unreasonably big and Dave had a problem with figuring out how it would be possible for him to fit it all the way inside him. After thinking it through properly, Dave decided that for the safety of his ass he would use the smaller dildo provided. Then once he was used to some sort of stretch and his insides were slicked, he would attempt to ride the monster between his teddy’s fluffy thighs. Uncapping the new bottle of lube, Dave poured enough on his hands to slick his whole fist up, laying between his bear’s legs as he spread his own, rubbing the lubed up fingers against his hairless hole.

Dave has never been shy when it came to his sex life, or what little one he had. He would never lock his door and so he was caught endless amount of times with his hand wrapped around his cock or his slim fingers fucking into his ass. He wasn’t going to lie; when his brain was muddled up with all the arousal, he loved the anticipation of someone walking in and watching him get himself off, his thoughts going to further and darker places to where he would hope they would join in and fuck him until he would pass out. Dave almost drooled with the fantasy that the person would just keep going, fuck him raw while he was unconscious and leave him with a cum filled hole.

It was no surprise that two fingers slipped in easily, from the amount of times he had stuffed himself, his body must have been used to the feeling of being stretched. Either that or he had the easy slip from all the lube he had coated his hand with. While his hand was busy getting himself prepared for the small dildo lying next to his thigh, Dave shut his eyes and imagined his usual fantasy of riding his teddy bear, the bear just sitting still while he rode it. He couldn’t help the whimper that escaped his throat, turning his head on the bear’s furry thigh and licking the strap on, his free hand grasping it so he can angle the thick tip onto his tongue, the taste of silicone easily forgotten about as Dave suckled on it. His hole clenched down when Dave attempted a third finger, but from experience he knew that adding a little force was all it would take for his ass to relax around the new appendage. He wanted to be fucked already, his cock dripping with precum over his slim stomach being completely ignored, his brain too focused on sucking the massive strap on and filling his ass with as many fingers he can stuff in. It wasn’t about his cock right now; it was all about his sweet spot and how many times he can abuse it without crying or screaming.

There was a thump outside of his room but Dave didn’t bother to stop his ministrations or sucking his bear’s cock. Deeming himself stretched enough for the small dildo, Dave rolled over onto his stomach, slicking the dildo up with the remains of the wet lube from his hand and pressed the blunt tip against his twitching asshole. Since the cock wasn’t that big and it was smoother than his fingers, it was easy for it to slip inside, Dave grabbing onto the base of the dildo so he could push it as deep as it could go. Once the fake dick was settled to the hilt, Dave let out a much needed breath.

He could tell just by the way his hole twitched and was attempting to suck the small dildo in as much as it could go that it was too tiny for Dave to enjoy fully. It wasn’t deep enough to rub against Dave’s prostate, but it slid against the soft walls inside which Dave could handle for the moment, letting his rim squeeze around the toy. It would be a slow process before he would be able to fit the monster of a strap-on inside him. Dave kept a tight on the base of the dildo, pushing in and out slowly, letting the muscles get used to the feel of the silicone. “Haah, fuck.”

His arm was beginning to get pins and needles from laying on it, so Dave knelt up on his elbow and knees, keeping one hand on the base of the toy at all times. Fucking back on the dildo, Dave closed his eyes and sucked the tip of the bear’s faux cock back into his mouth, bobbing his head on the tip and loving every moment of it. His fantasy was coming to life, and while it wasn’t what he had fully envisioned, it was enough for his dick to drizzle precum and his eyes to roll back into his head. With every slow push of the toy into his ass, his balls tightened up like he was going to cum any moment. It wasn’t even touching his sweet spot yet it was the best fuck he’d ever had, but he was sure that the strap-on would be out of this world if a small thing like the dildo was making him tremble this much.

“ _Mm_ , hmm…” Gulping down on the tip inside his mouth, Dave sped the pace of his fucking, his hand pressing the dildo deep inside him before ripping it out halfway and pushing it back inside. He couldn’t help his hips from moving back like someone was behind him, fucking on the small shaft in his ass. He needed more, with every thrust of the dick inside him; it was amazing but not enough. He wanted his prostate to be abused over and over again while he laid there and took it, he wanted his throat to be sore from all the amount of screaming he had done while being thoroughly fucked. His own cock jerked under him, hitting on his toned stomach and leaving a small wet smear from the pre.

A few minutes went by of the fast pace Dave was thrusting the small dildo into his ass, but it was easy to see that he was getting messy, desperate for it and it showed. With the way his thighs were shaking, his hole squeezing the toy tightly because he didn’t want to cum yet, he wanted to let it all out while he sat down on the massive strap on. A thick glob on saliva slid down his chin from slurping at the giant fake cock in his mouth, gagging around it as Dave tried his best to fuck the dick into his throat and failing epically, but _fuck_ if the sounds weren’t sexy. He needed the strap on, and he needed it right now.

Pulling his head back, the fake member popped out of his mouth leaving behind a string of spit connecting to Dave’s bottom lip. He pulled the small dildo out of his ass and let it bounce on the bed while he collected the lube bottle once more and poured a generous amount onto his hand. With that, he rubbed all over the strap on, getting it nice and wet for him because Dave knew that it would be an experience whether it would be painful or pleasurable.

“You can do this, Dave. You’re not scared of taking dick.” Dave spoke out loud to himself, straddling the teddy bear once more and reaching back to rub the remains of the lube from his hand around and into his hole, getting it slick for the tip to be an easy entry. Taking hold of the massive strap on, Dave gulped and positioned it to rub against his ass. Now that it was close enough to pop inside, the sheer size of it was enough for Dave to blanche and think twice about what he was about to do. Yes he measured it up to his ankle earlier, but the tip wasn’t as thick, so hopefully it should be a problem.

With that thought in mind, Dave started to press the tip of the fake dick into his ass. And then he tried again. And again. It wasn’t going in. It was like his hole was saying ‘no way is that going inside me, I will break’ and just clenched every time the tip tried to breach.

He wanted to cry from the frustration.

But, knowing this would happen; Dave took a deep breath and picked up the lube bottle again. He lathered the tip with more lube and pressed his slim fingers, two from each hand, into his ass to wet it up inside and open it wide as he sat back down. “This time for sure, you _will_ fit. So help me God.”

The tip entered a small amount but it was easy to tell that it was going to hurt if he sunk anymore, but Dave bit his lip and kept sitting down. He was slick enough, nothing was going to tear, and he will get this _fucking_ cock in his ass. More of it slipped inside, and Dave had to moan through his teeth as his poor hole protested around his four fingers, trying to clamp down on the intruder. He was resilient and didn’t stop until the whole tip of the cock was in his ass, pulling his fingers out and letting his hole quickly clench down on the toy. “Fuh, _god_. Shit, fucking fuck.”

He had to grab his base of his cock and squeeze so he wouldn’t cum just yet, because this was something magnificent, and if he came now it would hurt more than it would feel good. He knelt there giving his muscles some time to relax before he moved again, just a simple roll of his hips to get his bearings on the full feel of the strap on. His hand quickly flew to the bear’s fluffy neck, wrapping his arm around it as he panted. It just tingled everywhere, leaving his legs with no feeling and he had to hold onto his bear to keep him up as he kept rolling his hips over and over again. Dave couldn’t help himself, he was addicted to the strap on and this was just the tip.

“Feels good, feels _fucking_ good.”

Dave held onto the bear as he attempted to sink down for more of that dick, just slipping a little more before his ass protested once more. He would do this, slow and steady. It took a while, waiting until his ass would relax enough for him to slip down a smidge more and waiting again because his ass would tighten. He was glad he couldn’t see his clock in this position because he would have gotten impatient with peering over at how long this was taking.

He had to keep his mind occupied, and so Dave slipped into his imagination again. He thought about the bear, what would happen if his childhood friend was alive, what would it do? Well, it’s a bear, it would have surely torn him to pieces but this was _Dave’s_ imagination and so he thought that the teddy would rub his back and let him take his time, nuzzle and kiss his face while Dave’s hole worked around that fat shaft. Dave purposely lifted the teddy’s limp arms and wrapped them around his slim waist, letting the beany paws barely touch his ass. With his time wasted in his head he had unconsciously slipped at least an inch into his ass, which was enough for the tip to ever so gently nudge his prostate. Dave couldn’t stop himself this time; a giant strap on in his ass that was so close to his sweet spot and prodding it occasionally, his balls drew up and his cock squirted cum between his and the bear’s stomach, matting the fur but Dave gave no shits.

His thighs were trembling and he couldn’t stop moaning; loud, whorish moans radiating through the room. He would have been embarrassed if it weren’t for the best orgasm he’s ever had. He wanted another, one just as good, maybe even better if the strap on was deeper and insistently rubbing against his prostate. He didn’t even know if he could have multiple orgasms but he was certainly going to try, grinding down on the toy with all his weight and rutting his cock against the drying cum on his bear’s furry tummy. A couple of inches slid in his ass with little tightening, which Dave was thankful for because now the ridges of the tip was settled neatly against his sweet spot, pressing down on it. It was like his ass had given up with resisting, letting Dave do whatever he wanted with the fake dick. “Want you deep inside.”

Dave even tried to bounce on the toy a little, slipping the cock out halfway before pushing himself down, he didn’t know how much of the cock he had gotten inside himself, glancing down between him and the bear. It wasn’t that impressive; he thought that maybe with all this stretching that he would have been most of the way down but he wasn’t even halfway. Still, he couldn’t complain because he felt amazing. He kept the gentle bouncing motion along with the grinding of his hips, Dave was in heaven.

“Fuck meee…” He leant forward and smushed his face into the bear’s neck while his lower body did all the work, whining low and moaning when the tip rubbed and bumped into his sweet spot. Which was a lot. The thickness made it easy for his prostate to be thoroughly ground down by the dick. Everything at the moment was beautiful.

“Yeah, yeah fuck me. Fuck. So good.” He couldn’t stop babbling to the bear while he wrapped his other arm around the fluffy neck, clinging to it for dear life while he rode the toy. Humping against the matted fur of the teddy’s stomach, Dave could feel he was getting closer to another climax, his own cock drizzling and pink from the overuse. He was going to cum all over this bear, and nothing right now could make him stop until he was satisfied.

“ _What the_ _fuck_ , Dave?”

Well, except for his brother walking in.


	2. Chapter 2

**Notes for the Chapter:**

> And here's chapter two! Have a good day guys!

“ _What the_ _fuck_ , Dave?”

Dave didn’t know how to explain; he was on top of his giant, childhood teddy bear with a strap on, riding it and loving every second of it, while another smaller dildo lay next to his feet, a lube bottle keeping the used toy company next to it. He really didn’t know what to say. “Uhh…”

As if Bro had no shame, he strode into the room to get a closer look at the scene in front of him, standing in front of Dave. Taking in everything; the bear, the dildo, the huge strap on, the lube and of course a naked Dave holding onto the bear. “So you got your old bear down from the attic, made it pretty and then decided to fuck it?”

“Um…” Well he couldn’t say _no_. But it wasn’t the whole story, and Dave really didn’t want to go into detail right now when he was just trying to have a second orgasm. Bro’s face was unreadable as always, but it was comforting that his brother wasn’t disgusted at him. Instead, Bro’s hand landed on Dave’s shoulder and pushed him down on the strap on, causing the boy to let out a loud moan as he slipped down a little, his hole already stretched to the limit. “Bro, Bro please stop. Ah God, _fuck_!!”

“You know I could hear everything through these thin walls? Practically every night you’re rubbing your cock, fucking your ass, and I could hear you’re adorable little cries.” Bro grinned as he landed his other and on one of Dave’s hips, forcing him to move them so his younger brother was trembling with the fullness of the strap-on, letting out pathetic whines as his prostate was bumped again and again. Dave couldn’t do anything but cling on tightly to his bear, tears filling his eyes from the overstimulation. Now that his brother was here, he didn’t have to hide his moans, not like he was trying before but now he had no shame.

Bro watched as Dave started to roll his hips on his own, grinding down on that fat strap-on and letting it abuse his sweet spot. His own cock was hard in his jeans and if Dave wasn’t going to stop, then he wouldn’t make him. Unzipping his fly, Bro pulled out his cock and gave it languid stokes as he enjoyed the show. “You like playing with your toys, baby boy?”

“ _Oh God_. Don’t say that…” Dave shuddered and quickly grabbed the base of his cock, squeezing it tight to stop himself from going over the brink. He didn’t want this to end it now that he could possibly get more dick action than the fake ones he’s been riding. Even if his brother was connected to it, a penis was a penis. Bro couldn’t stop the smirk from whipping across his face, letting his grip go from Dave’s shoulder and ran his fingers through those light blonde locks instead, tugging them lightly much to Dave’s pleasure.

Moving the unwanted items aside for now, Bro sat down on the bed admiring the view of his little brother’s face as he continued to pump his cock. It wasn’t every day that he got to see a cute little twink riding on a strap-on attached to a teddy bear. He pulled Dave’s hair enough that the teenager would have to tilt his head to the side to see Bro, unable to look away as the elder kept a steady pace of his stroking. “You like it when I talk like that, baby boy?”

“Nn, fuck.” Dave’s eyes rolled back into his head, cock twitching. He didn’t know he could love being teased like this until now; his hair being pulled around and the slight twinge of pain to sizzle into his pleasurable grinding, it was enough to drive anyone wild. “Please, Bro.”

“Just love being cared for my your stuffed teddies, don’t you sweetie?”

Bro stood up then, letting go of Dave’s hair so that he could tug his jeans down enough that they won’t be in the way of his cock and balls. He then grabbed his brother’s head again, bringing it closer to his crotch. He kept a gentle grip so that if Dave really didn’t want to, he could pull away at any time, instead Dave just let out a whine as the thick cockhead bumped his lower lip. “Stop, Bro please. I can’t take it. Ah–!“

Before Dave could say anything more, the tip of Bro’s member was already inside his mouth, and it wasn’t like he was going to refuse something like this. The actions of what they were doing, it was taboo but it turned him on, along with the small amount of degrading and baby talk, it was getting to the point where Dave couldn’t think of anything more addicting. Mouthing the tip of Bro’s cock and taking in the taste of a man; he was a lie when people said dicks taste salty, Bro was slightly musty but the more he rolled his tongue around the head, it just felt like wet flesh. It was better than sucking on a dildo, bobbing his head back and forth and enjoying the warmth in his mouth.

Bro ran is fingers through Dave’s soft locks, tugging on them and moving his hips. Those lips were worshipping him, if he knew that Dave was this adorable while sucking cock he would have gone into his room earlier. He wondered if Dave had some experience with servicing people, giving head when they wanted just to get his rocks off. “Love making your big brother feel good, don’t you baby boy?”

“ _Mmm_ …” Dave closed his eyes, moaning around Bro’s cock. He loved every moment of it, his own shaft twitching as his hips rolled so he could get the bear’s strap-on deeper inside him. With every swivel of his hips, the toy rubbed over his sweet spot. He wanted to take as much of Bro into his mouth but knew he had a vicious gag reflex and so he wasn’t swallowing as much of Bro as he would have liked. Hugging the teddy close, Dave worked his tongue around the tip of that fat dick, across Bro’s frenulum until the older man was moaning breathily.

He just wanted to cum but _fuck that_ if he was going to stop this now, it was too good for him to stop. Bro didn’t want it to end so soon either, thrusting his hips into his brother’s mouth and holding the back of his head so he couldn’t pull away, feeling the way that if he got too close to the back of Dave’s throat, it would constrict around the tip of his dick. It was heavenly. “Sucking me so good, sweetheart. Shit baby, bet you fucking wanted this to happen didn’t you? Moan real loud like a baby whore so your big Bro could come in and give you what you need.”

Dave couldn’t do anything but moan around Bro’s thick shaft, riding as much of the strap on without stretching his hole too wide. He loved it; a throbbing cock in his mouth and a massive toy in his ass that he could do anything to, roll his hips, bounce on it or just sit still on it and relish in the feel of being full. The names were being sent right to his dick, making it drip with precum, his balls drawing up. He tried everything, gripping the base of his cock or thinking about things that would turn him off but it was useless.

Bro was thrusting into his mouth, the taste getting tangy with every lick over the tip and the more he grinds his hips down. “You’re going to choke on your big brother’s cock, take me all the way down in your throat and cum so you have to swallow it all.”

That was it, he was cumming. Spurting wet on the teddy bear as Bro pushed his dick further in Dave’s mouth until it was hitting the back of his throat, making him gag. It felt like he couldn’t stop his cock from leaking as Bro continuously pumped his cock into Dave’s throat, choking and coughing on the fat flesh that blocked his windpipe, eyes tearing up. Finally, Bro tensed up and a grunt, holding Dave’s head so he couldn’t spit it out as he came a thick wad of cum, feeling Dave gurgle as he glanced down. The poor boy’s face was scrunched up, tasting what another man’s jizz is like, he didn’t want to swallow it; Bro’s cum was slimy and savoury all at the same time and Bro wasn’t going to let up. He gulped and retched around Bro’s cock. “Good boy.”

He let go and Dave gasped once air was available, coughing and rubbing his sore throat. He didn’t want to get off the strap on, he physically _couldn’t_. His body felt heavy and weak, hugging the bear like it was a lifeline and whined loudly because the strap on was so _big_ , and it was still inside him, causing the sensitive sweet spot to be abused. “Bro, help.”

Bro chuckled and stuffed his cock inside his trousers again, zipping up his fly before he lifted his younger brother off the sex toy, laying him down on the bed. “Get some sleep, you look like you need it. And when you need to get off, just call me and I’ll fuck you. You don’t need those toys when you got a real cock always ready to go.”

Dave scoffed but took Bro’s advice, nuzzling into his pillow and reached out a hand to run his fingers through the fluff of the teddy bear, hearing the door to his bedroom close behind Bro. “I’ll always have you to make me feel good, Bro.”

**Notes for the Chapter:**

> This is a finished work, I won't be continuing this I apologize if there was any confusion


End file.
